Drawing Chair Conformations and Ring Flips for Cyclohexane

Studying chair conformations is likely one of the trickiest visual topics in organic chemistry, perhaps second only to Fischer projections. Not only are you required to learn a 3-dimensional concept, but you also have to manipulate that 3-D molecule on 2-dimensional paper.

The average orgo student is not an artist, making this topic even trickier. In this article I’ll show you a few quick and simple tricks to help you easily draw the standard hexagon, chair conformations and ring flips for cyclohexane.

When it comes to exams, you won’t be graded on how ‘pretty’ your chair looks. Instead your professor will look for clarity and the ability to distinguish your axial and equatorial substituents.

Drawing the Cyclohexane Hexagon

If there’s one thing you learn in organic chemistry – it’s how to draw a hexagon. Many students try to draw the entire thing at once, but the poor hexagon tends to look drunk and wobbly.

Here’s my approach:

Draw 2 parallel lines

Place a dot above the upper opening and another below the lower opening

Connect the dots

Pretty? Not especially

But clear? Absolutely!

And that’s what really matters.

As you get better you can combine steps 2 and 3 by simply visualizing the location of the dots.

Drawing the Cyclohexane Chair Conformation

This is where the messiness and confusion arises. Most books will show a chair conformation slightly sideways, making it impossible to copy. Worse, it’s really difficult to show which substituents are axial vs equatorial.

‘Bowties’ as I like to call them, are ok for the computer generated chair conformation. Here is my simple version which my tutoring clients use on exams with great success.

Step 1:

Draw 2 parallel lines slightly offset from each other. Top left or top right will give you alternate chairs.

Step 2:

Place a dot above the upper opening, and another below the lower opening

Step 3:

Connect the dots

Kinda sounds like the directions for drawing a cyclohexane, doesn’t it?

But the chair confirmation doesn’t stop here. It’s important to understand how to position your substituents. And even more important to show what is axial and what is equatorial.

So let’s move on:

Step 4:

Identify the ‘up tip’ OR ‘down tip’ of your chair conformation, and draw a straight line up (up tip) or down (down tip) parallel to the y-plane. This is your first axial substituent.

The chair conformation has alternating axial up, axial down… so once you have that single axial substituent move on to..

Step 5:

Alternate your axial substituents up and down all the way around your cyclohexane

Every carbon on the chair conformation has 1 substituent axial and the other equatorial. If axial is up equatorial is down, if equatorial is up then axial is down.

Step 6:

Pick any ONE carbon and locate its axial substituent. Draw the equatorial substituent up or down, the reverse of the axial substituent. But unlike the axial line, this one will start on the carbon and form a slight angle outward of the chair drawing. Do NOT draw these straight in the x or y plane.

Adding substituents to your chair

This is my favorite part. I find students get so confused when they try to match the cyclohexane to the drawing.

I don’t!

All I care about matching are the numbers.

Start with a blank chair conformation. Number the carbons in your cyclohexane and in your chair.

Clockwise or counterclockwise doesn’t matter, as long as you use the same direction for both molecules.

Then simply compare.

Identify the carbon number for the first substituent, if it’s wedged add it to the up position.

If the substituent is dashed, add it to the down substituent (dashes down)

In using this trick you simply match the numbers and let your molecule quickly fall into place

Drawing a Ring Flip

The logic and reasoning behind the chair conformation ring flip will be discussed in my upcoming chair conformations video series. (stay tuned) However, drawing the ring flip doesn’t have to be as hard as students think.

Yes the flip happens when one molecule changes its conformation to another, but the key to drawing the flip successfully is to… Ignore the first chair!

Counter-intuitive, I know, but trust me this method works.

Once you have your first chair, determine if your parallel lines have upper right or upper left.

Draw another chair using the steps described above, but change the direction of your top line.

If your first chair has the upper line on the right, draw the second chair with the upper line left.

Ignore your first chair as you follow the rules for drawing and adding substituents.

Now for the fun part, determine the new location for the up-tip carbon by ‘pulling down’ your ‘up-tip’ or raising up your ‘down-tip’ Number your new chair, and play ‘match the numbers’.

If there’s a substituent up on carbon #1, it says up on carbon #1. If it’s down it stays down.

The only thing that changes with your ring flip is the location of axial and equatorial.

Remember this:

Up stays up, down stays down

Axial becomes equatorial and equatorial becomes axial

Hopefully you’ve been drawing chairs as you read this article. What do you think? does the idea of drawing chair conformations and ring flips still sound as scary as it used to? Let me know by leaving a comment below

not sure if anyone posted this already (didn’t read through all the comments), but your equatorial markings on a few of the chairs on the ‘middle’ interior carbons are directed in the wrong way…
for example, on the very last flipped configurational drawing, carbon #1 & #4 equatorial lines should be leaning to the opposite direction.

If you’re referring to the ones going straight forward or back then it actually doesn’t matter. In truth we’re trying to draw it exactly forward or back. But that wouldn’t show on paper, so we offset slightly to one side or the other. Similar to drawing a Newman Projection in eclipsed conformation. It’s directly behind but we offset to one side making it visible on paper

I’m a little confused about the numbering. For the upper left chair do you always number the carbon in the bottom right corner 1? Does it matter which carbon is carbon 1 as long as you keep things consistent when you do the ring flip?

In a ring flip the corner carbon is pulled down and the entire numbering system shifts. But as long as you keep your sequence clockwise or counterclockwise (keep the same as the pre-flip chair) you’ll be ok

Good question Jennifer. When you ring flip you have to pull the top carbon down. This moves every carbon over 1 position. So if the top carbon was 2, in the ring flip the bottom carbon will be 2. That means carbon 1 moved 1 position to the left in the drawing. Try this with your model kit and give every number a different color substituent